Uses
Lithium Dicyclohexylamide is used in processes for preparing 2-Dihalo-ribolactones as synthons for antiviral nucleosides via coupling reaction.
Reactivity Profile
Lithium Dicyclohexylamide performs as a strong base, allowing deprotonation of ketones, esters, aryl and allyl halides, alkyl dihalides, allenes, alkyl boron reagents, azulene and methylazulenes; used for the formation of formamides, glyoxylamides, oxomalonamides, and tartronamides.
Synthesis
Lithium Dicyclohexylamide could be prepared from the reaction of dicyclohexylamine with n-Butyllithium in hexanes and benzene at 0 °C; the solvent can then be removed under reduced pressure, and the resulting free-flowing solid can be dissolved in THF.
Both solution and solid are pyrophoric and air- and moisture-sensitive; also, the solid is spontaneously flammable in air. The reagent is corrosive and extremely destructive to tissues of the mucous membranes and the upper respiratory tract, eyes, and skin. Note that dicyclohexylamine is a suspected carcinogen and may cause chemical pneumonitis and pulmonary edema. Use in a fume hood.
References
1. Wilson, J. W.; Pelter, A.; Garad, M. V.; Pardasani, R. T 1993, 49, 2979.
2. Aldrich Chemical Co.; Material Safety Data Sheet.
3. Furlong, J. J. P.; Lewkowicz, E. S.; Nudelman, N. S. JCS(P2) 1990, 1461.
